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Tetracycline information


Tetracycline
tetracycline 2D skeletal
tetracycline 3D BS
Clinical data
Pronunciation/ˌtɛtrəˈskln/
Other namesTE/TET/TC/TCY[1]
AHFS/Drugs.comMonograph
MedlinePlusa682098
License data
  • US FDA: Tetracycline
Pregnancy
category
  • AU: D
Routes of
administration
By mouth
ATC code
  • A01AB13 (WHO) D06AA04 (WHO) J01AA07 (WHO) S01AA09 (WHO) S02AA08 (WHO) S03AA02 (WHO) QG01AA90 (WHO) QG51AA02 (WHO) QJ51AA07 (WHO)
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability80%
MetabolismNot metabolized
Elimination half-life8–11 hours, 57–108 hours (kidney impairment)
ExcretionUrine (>60%), feces
Identifiers
IUPAC name
  • (4S,4aS,5aS,6S,12aR)-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide[2]
CAS Number
  • 60-54-8 checkY
    64-75-5 (hydrochloride)
PubChem CID
  • 54675776
DrugBank
  • DB00759 checkY
ChemSpider
  • 10257122 checkY
UNII
  • F8VB5M810T
KEGG
  • D00201 checkY
ChEBI
  • CHEBI:27902 checkY
ChEMBL
  • ChEMBL1440 checkY
PDB ligand
  • TAC (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID7023645 Edit this at Wikidata
ECHA InfoCard100.000.438 Edit this at Wikidata
Chemical and physical data
FormulaC22H24N2O8
Molar mass444.440 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C[C@]1(c2cccc(c2C(=O)C3=C([C@]4([C@@H](C[C@@H]31)[C@@H](C(=C(C4=O)C(=O)N)O)N(C)C)O)O)O)O
InChI
  • InChI=1S/C22H24N2O8/c1-21(31)8-5-4-6-11(25)12(8)16(26)13-9(21)7-10-15(24(2)3)17(27)14(20(23)30)19(29)22(10,32)18(13)28/h4-6,9-10,15,25,27-28,31-32H,7H2,1-3H3,(H2,23,30)/t9-,10-,15-,21+,22-/m0/s1 checkY
  • Key:OFVLGDICTFRJMM-WESIUVDSSA-N checkY
  (verify)

Tetracycline, sold under various brand names, is an oral antibiotic in the tetracyclines family of medications, used to treat a number of infections,[3] including acne, cholera, brucellosis, plague, malaria, and syphilis.[3]

Common side effects include vomiting, diarrhea, rash, and loss of appetite.[3] Other side effects include poor tooth development if used by children less than eight years of age, kidney problems, and sunburning easily.[3] Use during pregnancy may harm the baby.[3] It works by inhibiting protein synthesis in bacteria.[3]

Tetracycline was patented in 1953[4] and was approved for prescription use in 1954.[5][6] It is on the World Health Organization's List of Essential Medicines.[7] Tetracycline is available as a generic medication.[3] Tetracycline was originally made from bacteria of the genus Streptomyces.[3]

  1. ^ "Antibiotic abbreviations list". Retrieved 22 June 2023.
  2. ^ "Tetracycline". PubChem. National Center for Biotechnology Information.
  3. ^ a b c d e f g h "Tetracycline". The American Society of Health-System Pharmacists. Archived from the original on 28 December 2016. Retrieved 8 December 2016.
  4. ^ U.S. patent 2699054A
  5. ^ Cite error: The named reference History was invoked but never defined (see the help page).
  6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 489. ISBN 9783527607495. Archived from the original on 2016-12-20.
  7. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

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Tetracyclines are a group of broad-spectrum antibiotic compounds that have a common basic structure and are either isolated directly from several species...

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Doxycycline

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Doxycycline is a broad-spectrum antibiotic of the tetracycline class used in the treatment of infections caused by bacteria and certain parasites. It is...

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The discovery of tetracycline engendered an enormous amount of litigation. In late 1958, the U.S. government charged Pfizer and American Cyanamid with...

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Lymecycline

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a tetracycline broad-spectrum antibiotic. It is approximately 5,000 times more soluble than tetracycline base and is unique amongst tetracyclines in...

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Tooth discoloration

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copper (green), nickel (green) and cadmium (yellow-brown). Antibiotics. Tetracycline and its derivatives are capable of intrinsic discoloration (discussed...

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Metalloprotease inhibitor

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It is believed that tetracyclines also effect MMP expression and proteolytic activity. Doxycycline is a semi-synthetic tetracycline that has been studied...

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Antimicrobial spectrum

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Broad-spectrum antibiotic: Ciprofloxacin, Doxycycline, Minocycline, Tetracycline, Imipenem, Azithromycin Extended-spectrum antibiotic: Ampicillin Narrow-spectrum...

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Demeclocycline

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Demeclocycline (INN, BAN, USAN, brand name Declomycin) is a tetracycline antibiotic which was derived from a mutant strain of Streptomyces aureofaciens...

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PBR322

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ampicillin resistance (AmpR) protein, and the gene tetA encoding the tetracycline resistance (TetR) protein. It contains the origin of replication of pMB1...

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Oxytetracycline

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Oxytetracycline is a broad-spectrum tetracycline antibiotic, the second of the group to be discovered. Oxytetracycline works by interfering with the ability...

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Tigecycline

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Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline class...

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Minocycline

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Minocycline, sold under the brand name Minocin among others, is a tetracycline antibiotic medication used to treat a number of bacterial infections such...

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Photodermatitis

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Hexachlorophene (found in some prescription antibacterial soaps) Tetracycline antibiotics (e.g., tetracycline, doxycycline, minocycline) Benzoyl peroxide Retinoids...

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Anaplasmosis

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also be used, including sanitizing surgical equipment after each use. Tetracycline drugs are the most common treatment for anaplasmosis, and can provide...

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Glycylcycline

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antibiotics derived from tetracycline. These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely...

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ATC code D06

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Oxytetracycline D06AA04 Tetracycline QD06AA52 Chlortetracycline, combinations QD06AA53 Oxytetracycline, combinations QD06AA54 Tetracycline, combinations D06AX01...

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Perioral dermatitis

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topical steroids, changing cosmetics, and in more severe cases, taking tetracyclines by mouth. Stopping steroids may initially worsen the rash. The condition...

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Antacid

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interact with several oral medications, including fluoroquinolone and tetracycline antibiotics, iron, itraconazole, and prednisone. Metal chelation is responsible...

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Peritonitis

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is the only fluoroquinolone that covers anaerobes. Tigecycline is a tetracycline that can be used due to its coverage of Gram-positives and Gram-negatives...

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Rocky Mountain spotted fever

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of people who are infected die as a result. Before the discovery of tetracycline in the 1940s, more than 10% of those with RMSF died. Fewer than 5,000...

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Antibiotic

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antibiotics was given as a monotherapy. For example, chloramphenicol and tetracyclines are antagonists to penicillins. However, this can vary depending on...

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Tooth whitening

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enamel from white mottling to yellow brown appearances. Tetracycline and minocycline. Tetracycline is a broad-spectrum antibiotic, and its derivative minocycline...

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Pathogen

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A structure of Doxycycline a tetracycline-class antibiotic...

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Chlortetracycline

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(trade name Aureomycin, Lederle Laboratories) is a tetracycline antibiotic, the first tetracycline to be identified. It was discovered in 1945 at Lederle...

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Kitasatospora aureofaciens

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Kitasatospora aureofaciens is a species of Kitasatospora, and the source of many tetracycline antibiotics. The organism was first isolated at Sanborn Field on the...

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Seal finger

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treated with antibiotics; however, as seal finger can be treated with tetracycline or similar antibiotics, the causative organism is most likely bacterial...

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